Spontaneous head-to-tail cyclization of unprotected linear peptides with the KAHA ligation

Florian Rohrbacher; Gildas Deniau; Anatol Luther; Jeffrey W. Bode

doi:10.1039/c5sc01774b

Spontaneous head-to-tail cyclization of unprotected linear peptides with the KAHA ligation

Chemical Science ◽

10.1039/c5sc01774b ◽

2015 ◽

Vol 6 (8) ◽

pp. 4889-4896 ◽

Cited By ~ 22

Author(s):

Florian Rohrbacher ◽

Gildas Deniau ◽

Anatol Luther ◽

Jeffrey W. Bode

Keyword(s):

Cyclic Peptides ◽

Mechanistic Study ◽

Coupling Reagents ◽

Head To Tail Cyclization

The α-ketoacid–hydroxylamine (KAHA) ligation enables the direct cyclization of unprotected peptides upon cleavage, without coupling reagents or purification of precursors. We report the synthesis of a library of 24 cyclic peptides and a detailed mechanistic study.

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Synthesis of cyclic peptides via efficient new coupling reagents

Peptides ◽

10.1007/978-94-011-0683-2_26 ◽

1994 ◽

pp. 95-96

Author(s):

A. Ehrlich ◽

S. Rothemund ◽

M. Brudel ◽

M. Beyermann ◽

L.A. Carpino ◽

...

Keyword(s):

Cyclic Peptides ◽

Coupling Reagents

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Synthesis of cyclic peptides via efficient new coupling reagents

Tetrahedron Letters ◽

10.1016/s0040-4039(00)74087-1 ◽

1993 ◽

Vol 34 (30) ◽

pp. 4781-4784 ◽

Cited By ~ 45

Author(s):

A. Ehrlich ◽

S. Rothemund ◽

M. Brudel ◽

M. Beyermann ◽

L.A Carpino ◽

...

Keyword(s):

Cyclic Peptides ◽

Coupling Reagents

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ChemInform Abstract: Synthesis of Cyclic Peptides via Efficient New Coupling Reagents (I), ( II).

ChemInform ◽

10.1002/chin.199348247 ◽

2010 ◽

Vol 24 (48) ◽

pp. no-no

Author(s):

A. EHRLICH ◽

S. ROTHEMUND ◽

M. BRUDEL ◽

M. BEYERMANN ◽

L. A. CARPINO ◽

...

Keyword(s):

Cyclic Peptides ◽

Coupling Reagents

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“Head-to-Tail” Cyclization of Hexapeptides Using Different Coupling Reagents

Liebigs Annalen der Chemie ◽

10.1002/jlac.199319930182 ◽

1993 ◽

Vol 1993 (5) ◽

pp. 497-501 ◽

Cited By ~ 15

Author(s):

Susanne Zimmer ◽

Eike Hoffmann ◽

Günther Jung ◽

Horst Kessler

Keyword(s):

Coupling Reagents ◽

Head To Tail Cyclization

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ChemInform Abstract: “Head-to-Tail” Cyclization of Hexapeptides Using Different Coupling Reagents

ChemInform ◽

10.1002/chin.199337287 ◽

2010 ◽

Vol 24 (37) ◽

pp. no-no

Author(s):

S. ZIMMER ◽

E. HOFFMANN ◽

G. JUNG ◽

H. KESSLER

Keyword(s):

Coupling Reagents ◽

Head To Tail Cyclization

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Head-to-tail cyclization and use of Cα-allyl ester protection improves the yield of cyclic peptides synthesized by the oxime resin method

Tetrahedron Letters ◽

10.1016/s0040-4039(00)61589-7 ◽

1993 ◽

Vol 34 (44) ◽

pp. 7031-7034 ◽

Cited By ~ 8

Author(s):

Afrodite Kapurniotu ◽

John W. Taylor

Keyword(s):

Cyclic Peptides ◽

Allyl Ester ◽

Resin Method ◽

Head To Tail Cyclization

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Head-to-tail cyclization for synthesis of naturally occurring cyclic peptides on organophosphous small-molecular supports

Organic Chemistry Frontiers ◽

10.1039/d1qo01362a ◽

2022 ◽

Author(s):

Haidi Li ◽

Junyou Li ◽

Jie Chao ◽

Zixin Zhang ◽

Chuanguang Qin

Keyword(s):

Liquid Phase ◽

Benzyl Alcohol ◽

Cyclic Peptides ◽

Naturally Occurring ◽

Head To Tail Cyclization

To achieve the head-to-tail cyclic peptides via the liquid-phase on-support cyclization and synergistic self-cleavage strategy, 4,4’-bis(diphenylphosphinyloxyl) diphenyl ketoxime (BDKO) and 4-diphenyl phospholoxy benzyl alcohol (DPBA) were designed and prepared as...

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